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. 2011 Sep 19;16(9):8041-52.
doi: 10.3390/molecules16098041.

Intramolecular C-H···O hydrogen bonding in 1,4-dihydropyridine derivatives

Marina Petrova  1 , Ruslan Muhamadejev, Brigita Vigante, Brigita Cekavicus, Aiva Plotniece, Gunars Duburs, Edvards Liepinsh
Affiliations

Intramolecular C-H···O hydrogen bonding in 1,4-dihydropyridine derivatives

Marina Petrova et al. Molecules. .

Abstract

The diastereotopy of the methylene protons at positions 2 and 6 in 1,4-dihydropiridine derivatives with various substituents has been investigated. NMR spectroscopy and quantum chemistry calculations show that the CH···O intramolecular hydrogen bond is one of the factors amplifying the chemical shift differences in the 1H-NMR spectra.

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Figures

Scheme 1
Scheme 1
Synthesis of compounds 1 and 2.
Scheme 2
Scheme 2
Synthesis of compounds 1e, 2e.
Figure 1
Figure 1
The calculated optimal conformations in compounds 1f, 1b and 2f, 2b.
Figure 2
Figure 2
Slice of 1H-NMR NOESY spectrum for compound 3b. More intense NOE is registered between NH and HA, showing preferable orientation toward the NH.
Figure 3
Figure 3
1H-NMR spectral data of D2O solutions of compound 3b at 25 °C.
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